Lawsuits: When the Wealthy Sue and Get Sued
The Million Dollar Question: A billionaire is furious about an unflattering magazine story and wants to sue for defamation. His own lawyers tell him the story is accurate and he will probably lose. He sues anyway. What is he most likely actually buying?
A) A retraction and a public apology
B) A large money judgment
C) Time, cost, and pain imposed on the publication — leverage, not victory
D) Nothing, because courts throw out weak cases right awayRead on for the answer.
Most people meet the legal system a handful of times in a life — a fender bender, a landlord dispute, maybe a divorce. For the wealthy, litigation is closer to weather: a constant condition they plan around, insure against, and occasionally summon on purpose. Having money makes you a target for lawsuits and also gives you a weapon most opponents cannot match. This piece is about both sides of that coin — how the rich use the courts as a tool, why deep pockets change the math of any dispute, and what happens when the person being sued is the one with the resources. The recurring theme is simple and a little uncomfortable: in civil litigation, staying power is often worth more than being right.
What it is
A lawsuit is a formal dispute resolved by a court, but that clinical description misses what litigation actually is in the hands of someone with money. It is a contest of endurance. Civil cases are slow, expensive, and grinding, and the side that can comfortably absorb years of legal bills has an enormous advantage over the side that cannot — regardless of who is in the right. That asymmetry is the whole story of wealth and the courts.
For an ordinary person, a lawsuit is a crisis. For a wealthy individual or company, it is a line item — a manageable cost that can be deployed strategically. This turns litigation into something broader than dispute resolution. It becomes a way to deter critics, to silence a former employee or spouse, to punish a business rival, to protect a reputation, or simply to force a negotiation onto more favorable ground. The courtroom is the stage, but the real action is the leverage created by the threat of a long, costly fight that one side can shrug off and the other cannot.
It helps to separate two roles the wealthy play. As plaintiffs, they use lawsuits offensively — to make something happen or stop something from happening. As defendants, they are on the receiving end of everyone else’s claims, because a person with visible assets is worth suing in a way a person without them is not. Most affluent people spend time in both chairs over a lifetime, and the tools that help in one role — money, patience, good lawyers — help in the other.
Who uses it
On the plaintiff side, the frequent users are people and companies with both something to protect and the means to fight: business owners in contract and partnership disputes, public figures guarding their reputation, founders tangled in ownership fights, and families litigating over trusts and inheritances. These are often repeat players — they have been through litigation before, they have lawyers on retainer, and they understand that the process itself is a form of pressure.
The defendant side is broader, because wealth attracts claims. Doctors face malpractice suits, executives face securities and employment claims, developers face construction and environmental disputes, and anyone prominent faces the occasional opportunistic suit betting they will pay to make it disappear. This is why the genuinely rich treat lawsuits as a permanent background risk and build defenses in advance — a subject explored in Asset Protection: How the Wealthy Reduce Exposure to Risk. The person with $20 million is simply a more attractive target than the person with $20,000, and everyone involved knows it.
There is also a distinct category of wealthy litigant who sues to send a message. The most famous modern example is investor Peter Thiel, who secretly financed a string of lawsuits against the news site Gawker after it had reported on his private life. One of those cases — brought by the wrestler Hulk Hogan — ended in a jury verdict of $140 million and, ultimately, Gawker’s bankruptcy. Thiel reportedly spent around $10 million funding the litigation. He was not a party to the case at all; he was a wealthy backer using someone else’s lawsuit to destroy a company he wanted gone. That is litigation as strategy, not as grievance.
Why they use it
The wealthy sue for the same reasons anyone does — to recover money, enforce a contract, right a wrong — but they also sue for reasons the rest of us rarely can afford to. Four motives come up again and again.
The first is deterrence. A reputation for suing, and for suing hard, discourages future challengers. If former employees know an NDA will be enforced to the letter and any breach met with a well-funded lawsuit, most will stay quiet. The threat does the work; the actual case rarely needs to be filed.
The second is silence. Litigation, and the settlements that end it, are among the most reliable ways to keep information private. A confidential settlement with a non-disclosure clause converts a public dispute into a sealed one, which is why so many uncomfortable matters — harassment claims, contract fights, personal disputes — vanish into paperwork the public never sees. Money buys the ending, and the ending comes with a gag.
The third is control. For someone accustomed to shaping outcomes, the courts are another arena in which to impose order — on a business partner, a publisher, a spouse. The fourth is principle, which is real but often overlaps with ego: a wealthy person who feels wronged may pursue a case past the point of any economic sense simply because they can, and because losing the fight would feel worse than paying for it. When you can afford to make a point, the point sometimes becomes the purpose.
How it works
The mechanics of litigation are where money quietly decides everything. Start with who pays the lawyers. Ordinary plaintiffs in injury cases typically hire lawyers on contingency — the lawyer takes a percentage of any recovery and nothing if the case loses — because they cannot pay by the hour. The wealthy usually pay hourly, which buys something contingency clients rarely get: a legal team that will fight every motion, chase every document, and keep going indefinitely, because the meter simply runs. Paying by the hour is a luxury that turns into a weapon.
Those hours are not cheap. At the top firms, senior partners now bill in the range of $2,000 to nearly $3,000 an hour, and a hard-fought case runs through thousands of hours across partners, associates, paralegals, and experts. A serious commercial dispute can cost seven figures before it ever reaches trial. For most people that number is disqualifying. For a wealthy litigant it is a cost of doing business — and, crucially, a cost the other side may not be able to match.
Then comes discovery, the pre-trial phase in which each side must hand over documents and answer questions under oath. Discovery is expensive and invasive, and a well-resourced party can use it to grind an opponent down — demanding vast troves of records, taking days of depositions, and running up the other side’s bills until settling looks cheaper than continuing. Discovery is also where cases are often won or lost: the Dominion Voting Systems defamation case against Fox News turned in large part on internal messages surfaced in discovery, and Fox ultimately paid $787.5 million to settle — the largest known defamation settlement in U.S. history.
Most cases never reach a jury. They end in settlement, and settlement is where wealth’s leverage cashes out. The party that can credibly threaten to litigate for five more years negotiates from strength, and the resulting deal — often sealed, often bound by an NDA — reflects staying power as much as merit. A newer wrinkle is litigation finance: outside investors who fund a lawsuit in exchange for a share of the winnings, which lets a plaintiff with a strong claim but shallow pockets borrow the staying power money normally provides. It is a booming industry precisely because endurance is the scarce resource that decides civil cases.
What it costs
The direct cost of serious litigation is measured in the hundreds of thousands to millions of dollars, and it scales with how hard both sides fight. A straightforward contract dispute settled early might run tens of thousands in fees. A contested case that goes through full discovery, motions, and trial routinely costs each side well into seven figures — and that is before any judgment or settlement is paid.
The judgments themselves, in the cases that go the distance, can be staggering. Johnny Depp’s defamation trial against Amber Heard ended with the jury awarding Depp a net of about $10.35 million. Writer E. Jean Carroll won $83.3 million in one of her defamation suits against Donald Trump, on top of an earlier $5 million verdict. These are the visible peaks; for every headline number there are thousands of quieter cases where the real cost was simply the years and the fees.
It is worth naming the other currency litigation spends: time and attention. A major case can consume a person for years — depositions, document review, strategy calls, the low hum of an unresolved threat. Even for someone who can write the checks without blinking, that drain is real, and it is one reason many wealthy litigants settle cases they could probably win. The money is affordable; the years are not always worth it.
Hidden costs and tradeoffs
The biggest hidden cost of suing is that a lawsuit is a public act, and publicity has a way of turning on the person who summoned it. The most reliable trap is the Streisand effect — named for a case in which an attempt to suppress a photograph of a celebrity’s home instead drew a flood of attention to it. Suing over an unflattering story guarantees that the story gets a second life, now attached to the news that its subject cared enough to litigate. The very act meant to bury information often exhumes it.
Discovery, the weapon described above, is a double-edged one. A plaintiff who opens a case also opens their own files: once you sue, the other side can demand your documents, depose you under oath, and probe the very facts you hoped to keep quiet. Wealthy litigants have talked themselves into disaster by filing suits that handed opponents a legal right to information they would never otherwise have obtained. Going on offense means dropping your own guard.
Then there is the reputational and personal weight of being seen as litigious. A person or company known for suing critics may win individual cases while losing the broader battle for public sympathy — and defendants, especially media organizations, sometimes fight precisely to avoid being seen as a soft touch. Litigation also has a way of metastasizing, spawning counterclaims, appeals, and satellite disputes that outlast the original grievance. What looked like a clean strike becomes a years-long entanglement, which is a close cousin of the reversals explored in Falls From Grace: Bankruptcies, Frauds, and Reversed Fortunes.
What people get wrong
The most common misconception is that a rich person can sue over anything and win. In defamation specifically — the arena where wealthy plaintiffs are most active — the law makes winning genuinely hard. Under the Supreme Court’s New York Times v. Sullivan standard, a public figure suing over a false statement must prove actual malice: that the publisher knew the statement was false or recklessly disregarded whether it was true. That is a demanding bar, and it means many defamation suits by prominent people are long shots from the start. Even Elon Musk, sued and suing over harsh words, learned that the line between a winnable and unwinnable case is drawn by these rules, not by who has more money.
The second misunderstanding is that meritless suits sail through unopposed. They increasingly do not. Thirty-three states and the District of Columbia now have anti-SLAPP laws — statutes designed to kill lawsuits that target protected speech quickly and cheaply, sometimes forcing the person who filed the suit to pay the defendant’s legal fees. Filing a weak defamation case in a strong anti-SLAPP state can backfire, ending fast and leaving the plaintiff with the bill.
The deepest error, though, is thinking that “winning” a lawsuit means a courtroom victory. For a wealthy litigant, victory is usually the leverage the case creates long before any verdict — the settlement extracted, the silence purchased, the critic deterred. This is the trap in the opening question. The billionaire suing over an accurate story that he will probably lose is not really buying a judgment. He is buying the other side’s time, cost, and discomfort, hoping the mere expense of defending will produce a retraction, a settlement, or a chilling silence. The lawsuit is the message, and sometimes the message lands even when the case does not.
Bottom line
The answer to the Million Dollar Question is C: what the billionaire is most likely buying is not a win but leverage — time, cost, and pain imposed on the publication, in the hope that the fight itself produces the outcome the verdict never would. That is the essential logic of wealth and the courts. Litigation, for those who can afford it, is less a search for justice than an exercise of staying power, and staying power is the asset that decides most civil disputes.
The same leverage runs in both directions. It lets the wealthy go on offense — deterring, silencing, controlling — and it lets them defend themselves against the constant, opportunistic claims that visible money attracts. But the tool has real limits. Defamation law is hostile to famous plaintiffs, anti-SLAPP statutes punish weak suits, discovery exposes the one who filed, and the Streisand effect can turn a lawsuit into the very publicity it was meant to suppress. The people who use litigation best understand that a courtroom is a place where money buys endurance, not certainty — and that the smartest move is often the boring one the rest of this site keeps returning to: arrange your affairs so that when the suit lands, you are hard to reach and easy to defend, not scrambling to fight a war you started on someone else’s terms.
Related reading: Asset Protection: How the Wealthy Reduce Exposure to Risk · Reputation: How the Wealthy Manage Image, Exposure, and Scandal · Privacy: Why the Wealthy Value Invisibility · Falls From Grace: Bankruptcies, Frauds, and Reversed Fortunes · Divorce: What Happens When Wealth Splits
